10.1021/om0502279.s001 Yumei Luo Yumei Luo James W. Herndon James W. Herndon Tandem Isobenzofuran Formation−Diels Alder Reactions in the Coupling of Carbene Complexes with 2-Alkynylbenzaldehyde Derivatives Featuring an Alkyne-Dienophile Tether American Chemical Society 2005 intramolecular Carbene Complexes reaction proceeds hydrophenanthrene derivatives carbene complexes heterocyclic analogues oxanorbornene ring 2005-06-20 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Tandem_Isobenzofuran_Formation_Diels_Alder_Reactions_in_the_Coupling_of_Carbene_Complexes_with_2_Alkynylbenzaldehyde_Derivatives_Featuring_an_Alkyne_Dienophile_Tether/3281464 The coupling of carbene complexes and 2-alkynylbenzaldehyde derivatives has been examined for systems where the alkyne is further linked to an alkene. This reaction proceeds via generation of an isobenzofuran followed by a stereoselective intramolecular Diels−Alder reaction, followed by opening of the resulting oxanorbornene ring. A variety of hydrophenanthrene derivatives and heterocyclic analogues have been produced in this reaction. In one case the intramolecular Pauson−Khand reaction is a competing process.